New Search
Save
Sort
Used 2020 Toyota Highlander for Sale in Chicago, IL
Highlanders for Sale at Dealers, Ranked by CoPilot AI ?
Filters
Price
Year
Mileage
Trim
1
Price Drop
2021 Toyota Highlander XSE AWD • Milwaukee, WI
$35,992 • 27.4k miles
•••
#1 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $498 Price Drop
- Great Price - $3,719 Below Market
- Includes $1,903 Premium Upgrades
See more about this car
2
Price Drop
2021 Toyota Highlander XLE AWD • Northbrook, IL
$33,490 • 30.1k miles
•••
#2 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- $510 Price Drop
- Great Price - $2,680 Below Market
- Includes $832 Premium Upgrades
See more about this car
3
2021 Toyota Highlander XSE AWD • Brookfield, WI
$36,009 • 38.3k miles
•••
#3 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $2,404 Below Market
- Includes $1,344 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
4
2021 Toyota Highlander XSE FWD • Elmhurst, IL
$34,449 • 24.7k miles
•••
#4 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $4,200 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
- Motivation to Negotiate - Increasing
See more about this car
5
2021 Toyota Highlander XSE AWD • Milwaukee, WI
$34,540 • 51.5k miles
•••
#5 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A+” Buy
- Great Price - $2,337 Below Market
- Includes $1,318 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
6
2019 Toyota Highlander Hybrid XLE AWD • Northbrook, IL
$29,490 • 77.8k miles
•••
#6 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Great Price - $3,418 Below Market
- CARFAX: Clean Title, Not a rental or commercial vehicle
- Motivation to Negotiate - Increasing
See more about this car
7
Price Drop
2021 Toyota Highlander Hybrid Platinum AWD • Gurnee, IL
$37,995 • 57.2k miles
•••
#7 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $230 Price Drop
- Great Price - $2,961 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
8
Price Drop
2021 Toyota Highlander XLE AWD • South Bend, IN
$33,006 • 49k miles
•••
#8 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $425 Price Drop
- Great Price - $2,546 Below Market
- Includes $818 Premium Upgrades
See more about this car
9
2021 Toyota Highlander XLE AWD • Chicago, IL
$35,732 • 23.1k miles
•••
#9 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Good Price - $2,052 Below Market
- Includes $1,311 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
10
Price Drop
2021 Toyota Highlander XLE AWD • Mt Pleasant, WI
$34,597 • 32.8k miles
•••
#10 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $393 Price Drop
- Good Price - $1,857 Below Market
- Includes $832 Premium Upgrades
See more about this car
11
Price Drop
2019 Toyota Highlander XLE AWD • Michigan City, IN
$24,956 • 92.1k miles
•••
#11 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $544 Price Drop
- Great Price - $1,771 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
12
Price Drop
2021 Toyota Highlander XSE AWD • Milwaukee, WI
$37,590 • 23.8k miles
•••
#12 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $1,010 Price Drop
- Good Price - $1,725 Below Market
- Includes $1,344 Premium Upgrades
See more about this car
13
Price Drop
2021 Toyota Highlander Limited FWD • Milwaukee, WI
$36,995 • 19.8k miles
•••
#13 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $62 Price Drop
- Good Price - $1,587 Below Market
- Includes $1,054 Premium Upgrades
See more about this car
14
Price Drop
2019 Toyota Highlander XLE AWD • Streamwood, IL
$24,490 • 103.7k miles • Certified
•••
#14 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $300 Price Drop
- Great Price - $1,579 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
15
Price Drop
2021 Toyota Highlander XSE AWD • Milwaukee, WI
$37,588 • 32.8k miles
•••
#15 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- $407 Price Drop
- Good Price - $1,399 Below Market
- Includes $1,344 Premium Upgrades
See more about this car
16
2021 Toyota Highlander XLE AWD • Romeoville, IL
$35,000 • 28.4k miles
•••
#16 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A” Buy
- Good Price - $1,091 Below Market
- Includes $832 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
17
Price Drop
2021 Toyota Highlander XLE AWD • Northbrook, IL
$33,490 • 37.7k miles
•••
#17 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $500 Price Drop
- Good Price - $2,133 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
18
2021 Toyota Highlander XLE AWD • Mishawaka, IN
$33,597 • 29.7k miles
•••
#18 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Good Price - $2,098 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
- Very Low Mileage
See more about this car
19
Price Drop
2021 Toyota Highlander XLE AWD • Northbrook, IL
$33,990 • 27.1k miles
•••
#19 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $500 Price Drop
- Good Price - $2,044 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
20
Price Drop
2020 Toyota Highlander XLE AWD • Chicago, IL
$30,715 • 47k miles
•••
#20 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Good Price - $1,746 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
- Motivation to Negotiate - Very High
See more about this car
21
Price Drop
2021 Toyota Highlander LE AWD • Oak Lawn, IL
$29,900 • 35.7k miles
•••
#21 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $100 Price Drop
- Good Price - $1,725 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
22
Price Drop
2021 Toyota Highlander XSE AWD • Palatine, IL
$34,996 • 46.9k miles
•••
#22 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $803 Price Drop
- Good Price - $1,688 Below Market
- Includes $1,331 Premium Upgrades
See more about this car
23
Price Drop
2021 Toyota Highlander XLE AWD • North Aurora, IL
$35,999 • 17.5k miles
•••
#23 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $1,000 Price Drop
- Good Price - $1,619 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
24
2021 Toyota Highlander XLE AWD • Milwaukee, WI
$33,950 • 45.6k miles
•••
#24 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- Good Price - $1,592 Below Market
- Includes $1,377 Premium Upgrades
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
25
Price Drop
2020 Toyota Highlander LE AWD • Fox Lake, IL
$30,000 • 19.5k miles
•••
#25 2019-2021 Toyota Highlander
CoPilot AI: It’s an “A-” Buy
- $253 Price Drop
- Good Price - $1,566 Below Market
- CARFAX: One Owner, Clean Title, Not a rental or commercial vehicle
See more about this car
2020 Toyota Highlander
Mid-size Crossover
Seats
7
Fuel Economy
36 - 36City MPG
35 - 35Hwy MPG
NHTSA Rating Summary
Copilot Rating
Dimensions
Most Popular Models like HighlanderToyota Highlander near Chicago, ILOther Years
Why Use CoPilot?
Shop and buy your next car with confidence. CoPilot searches every car at every dealer, every day, and ranks them based on what matters to you.
When you shop for a new or used car, CoPilot helps you know more. We search every car at every dealer so you don't have to, we give you data and insights you won't find anywhere else, and we rank every car so it's easy to find the best car at the best price.
When you're ready to buy your next car, CoPilot helps you make sure you never get taken advantage of at the dealership. Would you like to know more than the salesperson? CoPilot helps you avoid any tricks, traps, and scams. Know how and what you can negotiate. With CoPilot, you'll save time, money, and frustration.